


Caught in His Webb

by mattzerella_sticks



Series: Season 15 Inspired [12]
Category: Supernatural
Genre: Accepting Sam Winchester, Angry Dean Winchester, Angry Sam Winchester, Bisexual Dean Winchester, Brotherly Angst, Brotherly Bonding, Chuck Bashing, Coming Out, Confessions, Dean Winchester Loves Castiel, Embarrassed Dean Winchester, Emotionally Hurt Dean Winchester, Hurt Dean Winchester, M/M, Mortality, Past Character Death, Past Relationship(s), Season/Series 15
Language: English
Status: Completed
Published: 2019-10-03
Updated: 2019-10-03
Packaged: 2020-11-22 12:08:31
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,329
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20873972
Author URL: https://archiveofourown.org/users/mattzerella_sticks/pseuds/mattzerella_sticks
Summary: When Sam met one of Dean's old hunting buddies - made during his time at Stanford - he didn't know what to expect.When said hunting buddy leaves, after finishing a hunt, and says goodbye with a chaste kiss - he doesn't know what to think.Can Sam get Dean to talk about his feelings? And will airing everything to dry help Dean understand and come to terms with more than what happened after the hunt?





	Caught in His Webb

**Author's Note:**

> Is it too early to start writing speculative fan fiction about Leo Webb and Season 15? YES! Do I care? No!
> 
> Here's to not looking like a clown when episode 7airs *fingers crossed*
> 
> *EDIT* Nothing's changed, just added it to my s15 coda series. Although this is DEFINITELY not what's going to happen this episode, it was good while it lasted :)
> 
> *SECOND EDIT* I was so wrong about Leo's character... like he is the COMPLETE OPPOSITE of what I wrote... Jinkies...

Sam watches Leo’s truck drive off, waiting until the cherry red Ford disappears around the corner before turning to Dean. His brother putters around the motel packing. Face hidden but flushed neck still burning minutes after Leo left. He isn’t surprised Dean bounces off the walls, especially with the explosive farwell Leo dropped on their laps.

“_ Maybe in another lifetime… we could’ve had something good. _”

A cheek kiss isn’t the most suggestive gesture, except the only time Dean’s seen a man’s lips close in on his brother’s face was in the heat of battle. Creatures snarling as they fight against whatever shield or restraint that blocks them from tearing into his brother’s face. Nothing as soft, innocent, or _ intimate _as a featherlight press against stubble.

“Dean -”

“We better get a move on Sammy,” Dean cuts him off, zipping up his duffel, “if we leave now we can probably skip an extra night on the road.”

Sam frowns, brows pinching tighter than a rubber band. “Dean… we need to talk.”

Dean’s hands pause from where they rest on the handles. His shoulders stiffen, enough that Sam doesn’t need to see his face to know his dimples are on full display. “Talk about what?” he asks. Gruff, tone warning Sam that if he chooses to travel down this road it’ll be filled with bumps, potholes, and traffic.

Luckily he knows all of Dean’s shortcuts.

“Leo was a pretty swell guy,” he starts, leaning against the wall.

Dean, thrown off like Sam planned, finally sneaks a peek. A fog of wariness clouds his gaze, as expected. “Yeah,” he says, “Glad to see the years don’t really change a guy…”

“So he was like that when you knew him?”

“Not exactly,” Dean says, “Was a lot less responsible, then again he wasn’t in _ charge _ of a whole camp. Just volunteered there a few times a week. More so in the summer… once it felt like I didn’t see him for two weeks when I was in town ‘cause he was putting in extra hours. I always felt like the bad influence, telling him to take time for himself so me and him could…” The smile slowly blossoming on his face withers away in the next moment as Dean catches onto Sam’s ploy. “No.”

“Dean -”

“I said no, Sam.” he barks, ripping open his duffel once more, “I don’t want to talk about our history, don’t care how much _ you _ want to.”

“_ Our _?”

“Our _ what _?”

“You said our,” Sam smirks, “As in your’s and his… meaning there _ is _ history.”

“So?” Dean asks, attempting to play cool even as his shaky fingers give him away, “you and I got a past. That’s _ our _ history. Don’t know why you have to say it like that ‘bout me and Leo.”

“Because _ our _ history isn’t… _ your’s _ and _ Leo’s _ history.”

Dean digs further into his bag, messing with the already perfect packing. Unfolding jeans and wrinkling shirts, tossing guns and blades like they were wadded balls of paper instead of weapons. Sam huffs, pushing off the wall and gliding towards his brother. He takes the plaid shirt from Dean’s hands - knuckles pale, freckles pronounced - and sets it to the side.

“C’mon, Sam,” he says, voice trembling, “we can’t waste any time…”

“Dean. _ Please _.”

The plaintive notes Sam spoke jar with Dean, tipping him over the edge. He shoves Sam away and roars, “What do you want me to say, huh? What do you want from me!”

“I want you to tell me the truth,” Sam says, “I want you to know that whatever _ that _ is… I’ll accept it.”

Dean challenges Sam with a long bout of silence, unaware to the lengths of awkwardly charged silence he’s willing to suffer through. Showing nothing but honest affection, Sam waits for his brother to fold. He crumples like a napkin, fog turning to mist.

“Shit, Sammy,” Dean coughs, rubbing at his eyes, “Couldn’t you have pretended you didn’t notice?”

Sam shrugs, mouth stretched thin. “Pretty hard not to.”

When Dean pulls his hand away Sam at least won’t comment on the redness rimming his eyes. “Me and him had this thing, okay? Dad had gone off on his own when I stumbled across a haunting here in town… Leo was gonna be its next victim when I swooped in and ran the ghost in with my crowbar. And then when the ghost came after me he did the exact same thing…”

“I figured it’d be a one-and-done kind of deal. We salt and burn the bones and then we go off our separate ways except… Leo didn’t want to leave. If that bastard is one thing it’s kind… saw hunting as another way he could give back. Tried to talk him out of it, tell him that it wasn’t the glamorous job he was thinking but… he was stubborn. And I guess I was lonely.”

Sam nods. “You and him hunted together?”

“Whenever I was in Texas,” Dean continues, “I’d call him up and we’d handle a case here and there, then we’d drive back to his place and patch each other up. I taught him all I knew about hunting and… well, Leo opened my eyes to this whole other world I was missing out on, too.”

“Then it wasn’t…” Sam sifts for the right words, “A one time deal? Some kind of _gay_ _thing_?”

He can see Dean weighing the options, hands swaying from side to side as he compares. Thankfully Dean chooses and shakes his head. “Definitely more than that. We never put labels on it or anything… with me on the road all the time I didn’t want him wasting away, waiting after me. Whenever we met up though… it was like the world didn’t exist. Of course, one day the pressure gives and it crashes back into you.”

“Dad hadn’t checked in in over a month, and not even Bobby or anyone else heard from him. All we had was… Jericho, California.”

Sam tenses, reminded of ghastly women and burning ceilings. He thought he put that town far back in the rearview mirror, so much so it wasn’t even a speck. But as this year has proven, nothing can stay buried in the past for long. Like the aftereffects from that simple hunt years ago still shake the very foundations of his and Dean’s relationship. Swallowing around the stone in his throat, he asks, “When you came to get me?”

Dean hums, a tight-lipped smile fixed to his face. “I wasn’t planning on coming alone,” he admits, “I was with Leo, getting ready to hit the open road again when I… I guess I was feeling bold. Or maybe cocky… I don’t know. Something made me ask him if he thought about coming along, to help.”

Stunned, Sam unconsciously moves away from Dean. Wobbles with spinning vision, as if learning what could have been was enough to fell his oak-like stature. His mind races at the possibility of Dean showing up in his apartment with Leo in tow, both there to whisk him away to find John. How different the road so far would be. The worst possibility Sam imagines sends shivers racing up his spine. Where the max occupancy remains two, except it’s Leo taking the shotgun seat instead of Sam. Sam washes his hands of any responsibility for John and sends Dean off with a half-hearted goodbye. An apocalyptic decision, he thinks, given the only reason the world’s been kicking for so long is because of them and the friends they’ve gathered.

He clears his mind of the what-ifs, reminding himself that they don’t matter since he and Dean went to Jericho, alone. They didn’t find their father but they finished his mission. He lost Jess… but he found his brother.

Sam focuses on the present and his brother’s uninterrupted rambling. “...a mess, though. Like, what if dad was in Jericho? Leo wasn’t ashamed of who he was… dad would’ve known in a heartbeat what was going on between us. Doesn’t matter now, though, since Leo said no.”

“Why did he?”

“Texas was one thing,” Dean smirks, gazing at a point beyond Sam, “California was another. Thought that by me asking for him to come with I was really asking for him to leave his old life behind which… in a way I was. When you’re a hunter, it's really hard to live half-in, half-out. Leo couldn’t cut the ties.”

“And what did you do?”

“What _ could _ I do?” he chuckles, “Tell him he was making a mistake? You saw his life… loving husband, great kids… I couldn’t give that to him. I swallowed down the hurt and left early in the morning, before he could wake up. With a note saying that he should forget about the life… and about _ me _ . Then I ditched my phone and picked up a burner on the way to meet… _ you _.”

Dean collapses onto the bed, uncaring to the mess he sits on. Gasping as he breathes for the first time without all that weight crushing his chest. Sam, at a loss for what to do, blindly reaches for his brother and squeezes his shoulder.

“Thank you for telling me all this, Dean,” Sam says, “I… I should’ve realized how close he was to you.”

The past few days make sense, the final piece fitting and highlighting the full picture. Dean’s awkwardness whenever they met up with Leo. His arms hung awkwardly at his side, no idea what to do with themselves. Over aware of their surroundings at all times, budgeting every word and movement like they were in short supply. Whenever Leo mentioned his family he jumped worse than a rabbit. How curt Dean became whenever Sam asked how he and Leo came to meet, offering only one or two words in explanation. Usually ‘no comment’. He figured there was hurt Dean kept hidden, but wouldn’t have guessed the cracks were in his _ heart _.

Dean snorts, running his wrist up his face. “No, you shouldn’t’ve. Leo was my first and _ last _. With him it felt like whatever anyone else thought didn’t matter, and when he was gone I… I locked the closet door behind me.”

Sam doubts that. With the floodgates open, memories pour into his awareness of times that Dean flexed the other half of his sexuality. How his eyes followed a mark a little too closely sometimes in the bar, leaning into them and blaming it on acting ‘drunk’. The snarky compliment here and there, masking the actual appreciation. Every time he deflected violently or made fun of Sam’s preferences weren’t the crumblings of Dean’s fragile masculinity. It was a scared boy, afraid that his younger brother was about to discover something he didn’t want getting out.

“Not even once?” he asks, “You know I wouldn’t have cared… right?”

His brother shrugs. “Yeah I knew. There were times I thought maybe I… could’ve said something. All those near-death experiences… and the _ actual _ deaths… I was never able to break through those walls though. Every opportunity was shadowed by the fear of _ dad _ finding out… even when it wasn’t possible. I’d lose all ability to talk and I… I’d freeze up like a deer in headlights. Kept me from saying a lot… _ doing _ a lot… being - being with…” Dean tucks his hands under his armpits, curling around himself.

The sudden pause draws Sam’s curiosity in, his mind leaping ten steps ahead to finish his brother’s thought. He tries to do so, attaching every possibility he can consider. ‘Being comfortable with himself’ isn’t a wild guess, but it makes no sense seeing how Dean was already this vulnerable with Sam. ‘Being with Leo’ tracked, given the lingering thread hanging between them. But he doubts Leo would trade the life he made for himself here, nor would Dean give up his life. He said before how proud he was of the journey they’ve traveled - all the people they helped and the wrongs they’ve righted - and Sam doesn’t doubt the conviction threading through those words.

Although he does consider what life Dean and Leo could have made together. Would Dean continue hunting every month, slowly weaning himself into retirement. If Leo was in Dean’s life could he have prevented some of the crazier things that have happened. His influence a calming force in their Winchester whirlwind?

Maybe with Leo Dean’s chance at normalcy would have succeeded? Waking up every morning with a pair of blue eyes to greet the morning.

It hits him like a lightning bolt.

“Dean,” Sam starts, “do you… you’ve felt this way about somebody else, right? Who wasn’t Leo.”

Dean rocks on the bed, unwilling to answer.

“Dean,” he whispers, “do you love Cas -”

“That’s enough!” He jumps forward, throwing Sam’s hand off of him. “We’re done with all this… touchy-feely crap. My skin’s starting to crawl…” he mutters, picking up the stuff he scattered with a fury. “You know I like guys, big whoop. That’s the only emotional doozy I’m sitting on so let’s get the show on the road, okay?”

Sam cannot turn away. They’ve made it this far, he needs to see this through. “You love him.”

“Sam, he’s our friend. He’s like a _ brother _ -”

“And you love him -”

“I did!” Dean shouts, rounding on Sam, “I did love him. _ Did _. Past tense… over and done. Meaning we don’t have to dive back into this bullshit. I felt it, I lived it… and I’ve gotten over it. Stacked it on a pyre and burnt the shit out of it. There’s nothing left to dissect but ashes, capisce?”

Given the grand display Sam finds it hard to believe. He stays silent though, the anger coursing through Dean’s gaze enough to char an iceberg. Sam retreats to his own bag. Cleaning in silence. A beat passes and Dean stomps to his duffle, shoving things inside.

They don’t speak to each other, and don’t need to.

Sam uses the time to reflect. On all the shared moments between his brother and the angel. Every charged exchange in the roller coaster of their relationship. From the highest peaks to the rocky lows. Remembers how friend and foe alike commented, reading more into what laid below the obvious surface. Again Sam figured they swung for low fruit in an attempt to rattle his brother. Actually they were striking closer to the heart.

The way Dean slammed Baby’s trunk reminds Sam of when Castiel died at Lucifer’s hands. When their friend’s grace dimmed, so did the light in Dean’s eyes. Returned only when he appeared in that alleyway. Dean’s face twitched, unable to smile. As if he forgot which muscles were used to lift the corners of his mouth. Or maybe was too scared that if he did Castiel would disappear in the next blink.

And therein lies the problem

“He’s as much in this as you are.”

Dean swerves, halfway out of the parking lot. Sam’s voice echoed in Baby’s cabin, the atmosphere too tense for any of Dean’s cassettes.

His brother squints at him, “What are you -”

“Cas,” Sam continues, “whatever logic you’ve used to convince yourself that he doesn’t love you back… it’s all wrong.”

Scowling, Dean completes the turn onto the main road. It takes one stop sign and two red lights for his brother to respond. “Who do you think you are, Mr. Know-It-All?”

“I _ think _ I’m the guy who’s had enough of his family falling apart and is yelling at the reason for it.”

“Me!” Dean shouts, “How is it my fault? Cas was the one who kept Jack’s soullessness under wraps. Who got mom killed -”

“Stow it, Dean.” Sam glares at his brother, shifting in his seat so Dean suffers the full force. “Cas isn’t the reason mom isn’t here. I know it, you know it - even _ mom _ knows it. What would she think if she knew you were acting like this to Cas?”

“But -”

“He thought he was doing what was right, and when he realized it wasn’t he _ apologized _ ,” Sam tells him, “You said you accepted it, but you still keep him at arm’s length. You barely speak to him unless it’s about a hunt. If it was really about mom, things would’ve gone back to normal but no - you’re _ afraid _ -”

“Maybe I have reason to be afraid, huh?” Dean snarls, clenching the steering wheel, “With Chuck abandoning - _for good_ \- us we have one shot. No more do-overs, no more hidden fixes. No kid to come by and shove another quarter into our slot, taking us into another level - none of it! And when things are on the upswing for us… that’s when the boot’s waiting to smush us. I can’t handle watching Cas die, again, Sam. The bastard’s more stubborn than you and I… he’ll go out in a blaze of glory before either of us. Where will I be then, huh? Mourning him all over? Wanting to die, again? Why shouldn’t I numb myself to that pain?”

Sam’s anger softens as Dean finally reveals the source of his problems. Worry lines add texture to Dean’s face, aging him severely. “So we have one shot,” Sam says, “now we’re no more special than anyone else. Good. You know how terrible it is being brought back again and again, Dean? Thinking you’ve found peace only to be shoved onto one last ride? With Chuck gone, it won’t be like that again. Finally we can choose how we end it.”

“Everyone ends up leaving me, Sam,” Dean whispers, tears pricking the corners of his eyes, “Cas always gets taken from me, just when I think I have him.”

“_ Chuck _ took him away,” he tells Dean, “Chuck was the one who did that. To make you suffer for… _ character development _ . Like he did with Jess, and Eileen… Bobby, Rufus, Ellen and Jo, Charlie… _ dad _ and _ mom _. We’re off the page now… it’s our life to live.”

“And die,” Dean says, staring into the open road as they leave the small Texas town, “Would it be more or less cruel if we die because of chance? If Cas gets unlucky during one fight?”

“Then wouldn’t it be worse to have loved him and _ not _ told him?” Sam asks, “Some of my biggest regrets are never telling Jess I loved her one last time… or asking Eileen to dinner… we need to make each second count this time around. So stop pushing us away and allow yourself to feel. It makes what little life we got left last longer.”

Sam, saying all he has to, faces the passenger window and waits. The flatlands go on for miles, blurring because of the speed Dean drives. They passed cattle and horse ranches, Dean not slowing down for either of them. He weaves through the traffic, a reactive driver even while stewing.

Overhead the sun dips, orange bleeding into the blue sky. They’re halfway through Oklahoma when Dean clears his throat.

“I love you, too, y’know,” he says, “Figured… if I’m gonna be saying it to Cas. And… don’t really know how many of those we’ll have left.”

Sam mirrors the tiny smile on Dean’s face. “I love you… _ no homo _.”

“Sam!”

“What?”

“Quit ruining the moment!”

“I just wanted to make it clear -”

“Oh like I’d ever get with you -”

“Some people want us, too. And you said you weren’t in love with Cas anymore…”

“I was trying to get you off my back -”

“Maybe I’ll see if Cas is interested in me? I think we’d be great together. We’ve been able to hang out _ a lot _since you’ve been avoiding him.”

“You touch him and I’ll drive us both into a canyon. I’ll end it right here, right now.”

“You wouldn’t do that, you love Baby too much!”

“If we’re both dead who’s going to drive her? Better she goes out with me than stolen by some spaz who won’t treat her right!”

They bicker while the sun sets, and well into the night.

**Author's Note:**

> What did you think? It got reaaallyy heavy towards the end... good soul-crushing stuff!
> 
> Drop a kudos/comment below!


End file.
